Eric BellIt feels like I’ve spent most of my life trying to keep track of stuff I want or need to do. From paper notes to digital lists to online syncing, from ephemeral to Sisyphean to obsessive to mindful, it’s been a journey.
Finding a system
To-do lists were always a lot of stuff. Writing down things to do, adding to the list, updating the list, reorganizing the list, losing the list, recreating the list. Keeping track of literal or metaphorical piles of notes and notions, in planners or folders or binders or boards.
My personal epiphany came when I was gifted a copy of Getting Things Done, by David Allen, after a particularly quirky but unsuccessful job interview in my temping days before grad school. That book’s subtitle, “the art of stress-free productivity,” held for me the same seductive appeal as the Hitchhiker’s Guide to the Galaxy’s mythical DON’T PANIC.
The GTD method (with its own schools of acolytes) came with a few distinctly insightful strategies:
- Capture everything. Getting outstanding tasks out of my head so that I just stopped spending constant mental energy trying to keep track of it all. Instead, I could write each thing down in a standard Inbox-like place and then relax, knowing I could predictably find it later.
- Regular review cadence. At the end of my day or so, go through my inbox and file everything into an appropriate list. At the end of a week or month, go through each of my project areas and update or order or just remember what’s next to do.
- Contextual lists. When reviewing or filing to-dos, group them and my broader projects into “areas” of my life. These contexts could then serve as triggers for surfacing relevant projects. For example, “school” or “workplace” or “[specific hobby]”. This aspect of GTD was the most challenging for me, both as a student and as the world moved into digital tools. My tasks were rarely dependent on physical context, I had no set work hours, and I could work on most of my projects in any space with a laptop and internet.
- Other pieces of the approach, like clarifying tasks into small actionable steps, or triaging quick tasks from bigger chunks of focus time, were less revolutionary to me at the time but nonetheless valuable.
The GTD approach provided a pragmatic mental framework for capturing, organizing, and maintaining a flexible large task list across various areas of my life and projects.
Finding the right tool
Having a method is great, but where would I actually put everything? From paper notebooks and bullet journals to a parade of software and apps, I spent years iterating through tools trying to find the right balance of structure and flexibility that works for me.
In high school it was paper planners, class handouts, and noticing that reminders in red ink stayed legibly on my hand longer than blue ink. In college it was a desktop of digital sticky notes, a binder for each semester, and a paper filing system. By grad school I had finally succumbed to my first cell phone and was switching from paper planners to digital calendars. Suddenly, accessing notes and tasks from multiple computers, browsers, and eventually my phone was key.
Some tools and their tradeoffs
- OmniFocus. Structured with GTD in mind, but just a few too many layers to get lost in.
- Todoist. Web-based and better cross-platform access, but too few facets.
- Things. More optimized for GTD, but at a time when I was trying Android and Windows phones, being constrained to Apple devices without even a web view was too limiting.
- Asana. Excellent for cross-team visibility and a useful view for each user. Overkill for an individual.
- Trello. The right balance of constraints and flexibility, with solid cross-platform compatibility. Trello’s main downside has been a lack of cross-board views. While it’s added some useful automations and syncing over the years, it still lacks a reliable way to see a meta-view of the top items in specific lists across boards.
Building habits one brick at a time
For such a long time, I would go through a cycle of getting frustrated with my current broken system, getting inspired to sketch out a new idea and approach, and then get bogged down making it happen in one big bang rollout.
Eventually I learned more about habit formation, mostly by way of the personal-professional cross-polination of designing for it. Shoutout to Nir Eyal’s talk at a “healthy habits” hackathon back in the day. Reducing hurdles to the intended workflow, making the desired action clear and intuitive, and otherwise adding nudges to do the next thing.
To improve my habit-building strategy, the key was small steps and iterating. I needed to start small rather than trying to change all of my behavior at once. So for me, that looked like a combination of…
- adding one small habit at a time (e.g., first get used to logging my sleep, then add what I ate for breakfast)
- putting a desired habit in my own path (e.g., my browser starts with Gmail and my food diary tabs open)
I eventually realized (shoutout to Nir Eyal, a case of personal-professional cross-pollination) that I needed to start with small triggers and nudges and loops to build up habits one sustainable piece at a time.
plan out or not
one small change
(a few coworkers over the years have commented that I’m the most organized person they know, but I still feel the imposter syndrome. This has been such as long slog of one-brick-at-a-time with occasional “raze it to the ground” moments. Admittedly, visualizing my organization system felt like a milestone of holistic thought-through-ness.)
balancing with work tasks
need for harmonious team coordination
personal vs team preferences (e.g. granularity, activity visibility)
team vs company preferences (e.g. designers Pivotal vs devs Jira)
Other insights
Done lists (personal accomplishment visibility, team review visibility). Introduced to the concept while at Viki, not as useful for team visibility later found it surprisingly useful for personal tasks Rather than simply archiving things when I finished them, I could move them into a regular list of done tasks (that might auto-archive itself periodically), which I could see growing and periodically glance at for a sense of accomplishment.